Organo silicon amides



Patented Aug. 19, 1952 ORGAN O SILICON AMIDES Leo Harry Sommer, State College, Pa., assignor to Dow Corning Corporation, Midland, Mich, a corporation of Michigan No Drawing. Application May 24, 1951,

7 Serial No. 228,122

3 Claims. (01. 260-4482) This invention relates to organosilicon amides and the methods for preparing them.

It is an object of this invention to prepare new compositions of matter which incorporate the properties of both siloxanes and polyamide resins. These materials are useful for coating compositions. I

This invention relates to a composition of matter having the formula (C1102 (011202] sucmncomawmnsw wherein n has an average value of at least 2.

The above compounds are prepared from substituted triorganosilylamide of the formula CH3) 2RSi CH2) 2CONH(C H2) 2Si (CH3) 2R where R is phenyl or methyl, by the method which comprises interacting the amide with concentrated sulfuric acid whereby the R group is cleaved from each of the silicon atoms to form a silyl sulfate ester (-SlOSOsH) and RH. This ester is then hydrolyzed to give a siloxane.

The above amide may be prepared by reacting an acyl chloride of the formula R(CH3) 2SiCH2CI-I2COC1 with B-triorganosilyl ethyl amine of the formula R(CH3) 2SiCH2CH2NH2 Example 1 250 cc. of anhydrous benzene and '73 grams of betatrimethylsilylethylamine were placed in a closed system equipped with a soda-lime tube. An atmosphere of nitrogen was maintained in the system as 51.3 grams of betatrimethylsilylpropionyl chloride was added dropwise. A white precipitate appeared instantly as each drop was added. The addition was complete in one hour. Approximately 30 cc. more of benzene was used to wash down the dropping funnel. Stirring was continued at room temperature for another 3 hours. The reaction mixture was poured into 400 cos. of water and the benzene layer separated. The aqueous layer was extracted with three 50 cc. portions of benzene and the combined benzene extracts were washed with two 100 cc. portions of 1 N HCl. The benzene layer was then washed with water until neutral. The benzene was re- 2 moved and the product was distilled to give a pale yellow oil of medium viscosity which boiled 132 to 132.5 C. at 2 mm. This represents a 93 per cent yield of the product N-(beta-trimethylsilylethyl) -beta-trimethylsilylpropionamide.

10 parts by weight of this compound was treated with 9 parts of concentrated sulfuric acid and allowed to stand at room temperature. Gaseous evolution began to take place within a few minutes and continued for about one-half hour. The flask was then heated on a steam bath for one hour longer. The reaction mixture was then added slowly to a solution of potassium hydroxide in absolute alcohol. The amount of hydroxide employed was sufficient to neutralize the sulfuric acid and the mixture was allowed to stand over night. The mixture was filtered and the alcohol was removed and the remaining viscous liquid was made slightly acid with HCl. Upon standing, the liquid became more and more viscous.

This material was a polymer of the formula (CH3) 2SiCI-I2CH2CONHCHzCI-I2Si (CH3) 20111 Example 2 The above results are obtained when the starting material for the process of Example 1 is a compound of the formula 1 C6H5 (CH SiCH CH CONHCH CH Si CH3) QCGHE That which is claimed is: 1. A method of preparing a polymeric siloxane of the formula [(CHs) 2SiCH2CI-I2CONHCH2CH2S1 (CH3) 2011:

where n has an average value of at least 2, which comprises reacting a compound of the formula R(CH3) 2SiCH2CH2CONHCH2CH2Si (CH3) 2R with concentrated sulfuric acid and thereafter hydrolyzing the material, in the above compound B. being selected from the group consisting of methyl and phenyl radicals.

2. (CH3)2SiCH CH CONHCHgCH Si(011102 1 where n has an average value of at least 2.

3. R(CH SiCH CHflONHCHZCHZSi(CHSMR where R'is selected from the group consisting of methyl and phenyl radicals.

LEO HARRY SOMMER.

No references cited. 

1. A METHOD OF PREPARING A POLYMERIC SILOXANE OF THE FORMULA 